1-Bromo-3-chloropropane → HCID 68576119, compound

HRID 272992Notes

Reaction equation

HRID 272992 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[CH3:6][N:7]([CH2:9][C:10]1([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:8].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:5][CH2:4][CH2:3][CH2:2][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2([CH2:9][N:7]([CH3:8])[CH3:6])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Product 1

HCID 68576119HCID 68576119, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

1-Bromo-3-chloropropane (0.42 ml, 4.25 mmol) was added to a solution of 4-(4-dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.0 g, 4.25 mmol) and potassium carbonate (1.5 g, 10.8 mmol) in N,N-dimethylformamide (10 ml). The reaction mixture was stirred at 45° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and water (50 ml). The organic layer was separated, dried over sodium sulphate, filtered and concentrated in vacuo to provide the title compound (800 mg, 60%). LRMS APCI+ m/z 412 [MH]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (100 ml) and water (50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-526fc2f819b94297a24949e048761f57
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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